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DE01981893T1 - IMPROVED METHOD FOR PRODUCING A GABAPENTIN INTERMEDIATE - Google Patents

IMPROVED METHOD FOR PRODUCING A GABAPENTIN INTERMEDIATE Download PDF

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Publication number
DE01981893T1
DE01981893T1 DE0001337506T DE01981893T DE01981893T1 DE 01981893 T1 DE01981893 T1 DE 01981893T1 DE 0001337506 T DE0001337506 T DE 0001337506T DE 01981893 T DE01981893 T DE 01981893T DE 01981893 T1 DE01981893 T1 DE 01981893T1
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Prior art keywords
product
preparation
compound
ammonium hydroxide
gabapentin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
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DE0001337506T
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German (de)
Inventor
Maria Stefania MONTANARI
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Teva Pharmaceutical Industries Ltd
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Teva Pharmaceutical Industries Ltd
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Publication of DE01981893T1 publication Critical patent/DE01981893T1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

Verfahren zur Herstellung einer Verbindung der Formel 1

Figure 00000001
bei dem man ein Keton mit Ethylcyanoacetat in der Gegenwart von Ammoniumhydroxid umsetzt.Process for the preparation of a compound of formula 1
Figure 00000001
in which a ketone is reacted with ethyl cyanoacetate in the presence of ammonium hydroxide.

Claims (29)

Verfahren zur Herstellung einer Verbindung der Formel 1
Figure 00010001
bei dem man ein Keton mit Ethylcyanoacetat in der Gegenwart von Ammoniumhydroxid umsetzt.Process for the preparation of a compound of formula 1
Figure 00010001
in which a ketone is reacted with ethyl cyanoacetate in the presence of ammonium hydroxide. Verfahren nach Anspruch 1, wobei das Keton Cyclohexanon ist.The method of claim 1, wherein the ketone is cyclohexanone is. Verfahren nach Anspruch 1, wobei die Umsetzung in einem wäßrigen Milieu stattfindet.The method of claim 1, wherein the implementation in an aqueous environment takes place. Verfahren nach Anspruch 1, welches weiterhin ein Lösungsmittel umfaßt.The method of claim 1, further comprising a solvent includes. Verfahren nach Anspruch 4, bei welchem das Lösungsmittel Methanol ist.The method of claim 4, wherein the solvent Is methanol. Verfahren nach Anspruch 4, bei welchem das Lösungsmittel Ethanol ist.The method of claim 4, wherein the solvent Is ethanol. Verfahren nach Anspruch 1, wobei die Umsetzung innerhalb von 24 Stunden im wesentlichen abgeschlossen ist.The method of claim 1, wherein the implementation within of 24 hours is essentially complete. Verfahren nach Anspruch 1, welches weiterhin die Zugabe von Wasser umfaßt.The method of claim 1, further comprising the Includes addition of water. Verfahren nach Anspruch 1, wobei das Verhältnis von Ethylcyanoacetat zu Cyclohexanon im Bereich von 1:0,5 bis 3:2 liegt.The method of claim 1, wherein the ratio of Ethyl cyanoacetate to cyclohexanone is in the range of 1: 0.5 to 3: 2. Produkt, hergestellt nach dem Verfahren von Anspruch 1.Product made by the process of claim 1. Verfahren zur Herstellung einer Verbindung der Formel 1, bei dem man Cyclohexanon und Ethylcyanoacetat in der Gegenwart von Ammoniumhydroxid umsetzt.Process for the preparation of a compound of formula 1, in the presence of cyclohexanone and ethyl cyanoacetate implemented by ammonium hydroxide. Produkt, hergestellt nach dem Verfahren von Anspruch 11.Product made by the process of claim 11th Verfahren zur Herstellung von α,α'-Dicyano-/β,β'-pentamethylenglutarimid, bei dem man Cyclohexanon und Ethylcyanoacetat in der Gegenwart von Ammoniumhydroxid umsetzt.Process for the preparation of α, α'-dicyano- / β, β'-pentamethylene glutarimide, in which Cyclohexanone and ethyl cyanoacetate in the presence of ammonium hydroxide implements. Produkt, hergestellt nach dem Verfahren von Anspruch 13.Product made by the process of claim 13th Verfahren zur Herstellung von Pentamethylenglutaramiden durch Ausführung der Guareschi-Reaktion in der Gegenwart von Wasser.Process for the preparation of pentamethylene glutaramides by execution the Guareschi reaction in the presence of water. Produkt, hergestellt nach dem Verfahren von Anspruch 15.Product made by the process of claim 15th Verfahren zur Herstellung von Pentamethylenglutaramiden durch Ausführung der Guareschi-Reaktion in der Gegenwart von Ammoniumhydroxid.Process for the preparation of pentamethylene glutaramides by execution the Guareschi reaction in the presence of ammonium hydroxide. Produkt, hergestellt nach dem Verfahren von Anspruch 17.Product made by the process of claim 17th Verfahren zur Herstellung von Glutaramiden durch Ausführen der Guareschi-Reaktion in der Gegenwart von Wasser.Process for the preparation of glutaramides by To run the Guareschi reaction in the presence of water. Produkt, hergestellt nach dem Verfahren von Anspruch 19.Product made by the process of claim 19th Verfahren zur Herstellung von Glutaramiden durch Ausführung der Guareschi-Reaktion in der Gegenwart von Ammoniumhydroxid.Process for the preparation of glutaramides by execution the Guareschi reaction in the presence of ammonium hydroxide. Produkt, hergestellt nach dem Verfahren von Anspruch 21.Product made by the process of claim 21st Verfahren zur Herstellung einer Verbindung der Formel 1, wobei das Verfahren die Umsetzung eines Ketons mit wenigstens einem Ester von Cyanoessigsäure umfaßt.Process for the preparation of a compound of formula 1, wherein the method involves the reaction of a ketone with at least an ester of cyanoacetic acid includes. Verfahren nach Anspruch 23, wobei der wenigstens eine Cyanoacetatester Methylcyanoacetat ist.The method of claim 23, wherein the at least a cyanoacetate ester is methyl cyanoacetate. Gabapentin-Verbindung, hergestellt aus dem Produkt von Anspruch 10.Gabapentin compound made from the product of claim 10. Gabapentin-Verbindung, hergestellt aus dem Produkt von Anspruch 12.Gabapentin compound made from the product of claim 12. Gabapentin-Verbindung, hergestellt unter Verwendung des Produkts von Anspruch 14.Gabapentin compound made using the product of claim 14. Gabapentin-Verbindung, hergestellt unter Verwendung des Produkts von Anspruch 16.Gabapentin compound made using the product of claim 16. Gabapentin-Verbindung, hergestellt unter Verwendung des Produkts von Anspruch 23.Gabapentin compound made using the product of claim 23.
DE0001337506T 2000-11-02 2001-10-26 IMPROVED METHOD FOR PRODUCING A GABAPENTIN INTERMEDIATE Pending DE01981893T1 (en)

Applications Claiming Priority (3)

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US24489100P 2000-11-02 2000-11-02
US244891P 2000-11-02
PCT/US2001/042783 WO2002036545A1 (en) 2000-11-02 2001-10-26 Improved process for production of gabapentin intermediate

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DE01981893T1 true DE01981893T1 (en) 2004-05-19

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EP (1) EP1337506A4 (en)
JP (1) JP2004530637A (en)
KR (1) KR20030048105A (en)
CN (1) CN1471507A (en)
AU (1) AU2002213506A1 (en)
CA (1) CA2427237A1 (en)
CZ (1) CZ20031432A3 (en)
DE (1) DE01981893T1 (en)
ES (1) ES2209674T1 (en)
HR (1) HRP20030443A2 (en)
HU (1) HUP0303352A3 (en)
IL (1) IL155733A0 (en)
IS (1) IS6799A (en)
MX (1) MXPA03003899A (en)
NO (1) NO20031927D0 (en)
PL (1) PL365569A1 (en)
SK (1) SK6372003A3 (en)
WO (1) WO2002036545A1 (en)
YU (1) YU33303A (en)
ZA (1) ZA200303349B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050004219A1 (en) * 2003-07-01 2005-01-06 Medtronic, Inc. Pump systems including injectable gabapentin compositions
US20050090549A1 (en) * 2003-10-23 2005-04-28 Medtronic, Inc. Intrathecal gabapentin for treatment of pain
US20050090548A1 (en) * 2003-10-23 2005-04-28 Medtronic, Inc. Intrathecal gabapentin for treatment of epilepsy
US20050187295A1 (en) * 2004-02-19 2005-08-25 Surendra Kalyan Processes for the preparation of gabapentin
ITMI20040501A1 (en) * 2004-03-17 2004-06-17 Caffaro Spa Ind Chim PROCEDURE FOR THE PREPARATION OF THE MONOAAMIDE OF THE CYCLOSENDIACETIC ACRID
ITMI20041271A1 (en) * 2004-06-24 2004-09-24 Zambon Spa GABAPENTINA PREPARATION PROCESS
CN100341856C (en) * 2005-08-19 2007-10-10 江苏恩华药业集团有限公司 Gabapentin hydrochloride preparing process
US8495974B2 (en) 2009-05-18 2013-07-30 Vito Agosta Fuel system and method for burning liquid ammonia in engines and boilers

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1142168B (en) * 1959-07-01 1963-01-10 Warner Lambert Pharmaceutical Process for the production of ª ‰, ª ‰ -Penta-methylenebutyrolactone or salts of 3, 3-pentamethylene-4-hydroxybutyric acid
DE2460891C2 (en) 1974-12-21 1982-09-23 Gödecke AG, 1000 Berlin 1-aminomethyl-1-cycloalkaneacetic acids and their esters, processes for their preparation and medicaments containing these compounds
DE3928182A1 (en) 1989-08-25 1991-02-28 Goedecke Ag METHOD FOR PRODUCING GABAPENTIN
IL125544A (en) * 1996-03-14 2002-03-10 Warner Lambert Co Substituted cyclic amino acids and pharmaceutical compositions containing them

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HUP0303352A3 (en) 2005-04-28
EP1337506A4 (en) 2005-05-04
IL155733A0 (en) 2003-11-23
CA2427237A1 (en) 2002-05-10
JP2004530637A (en) 2004-10-07
CN1471507A (en) 2004-01-28
NO20031927L (en) 2003-04-29
US20020107395A1 (en) 2002-08-08
KR20030048105A (en) 2003-06-18
US6881843B2 (en) 2005-04-19
EP1337506A1 (en) 2003-08-27
WO2002036545A1 (en) 2002-05-10
CZ20031432A3 (en) 2003-12-17
SK6372003A3 (en) 2003-12-02
MXPA03003899A (en) 2005-02-17
PL365569A1 (en) 2005-01-10
ES2209674T1 (en) 2004-07-01
AU2002213506A1 (en) 2002-05-15
YU33303A (en) 2006-05-25
ZA200303349B (en) 2005-06-09
US20030195358A1 (en) 2003-10-16
IS6799A (en) 2003-04-30
HRP20030443A2 (en) 2005-04-30
US6613904B2 (en) 2003-09-02
NO20031927D0 (en) 2003-04-29
HUP0303352A2 (en) 2004-01-28

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